Triethylamine → (E)-4-[3-(3-thienyl)phenyl]-3-buten-2-one

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:12](O)[CH2:13][C:14](=[O:16])[CH3:15])[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.CS(Cl)(=O)=O.C(N(CC)CC)C>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8](/[CH:12]=[CH:13]/[C:14](=[O:16])[CH3:15])[CH:9]=[CH:10][CH:11]=2)=[CH:2]1

Participants

Procedure

The resulting alcohol compound was dissolved in 2 ml of ethyl acetate, and 207 mg of methanesulfonyl chloride and 366 mg of triethylamine were added. The mixture was stirred overnight at room temperature, and then the precipitate was removed by filtration. The filtrate was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=5/1] to give 327 mg of the captioned compound as a pale yellow powder.